The present invention relates to organosilicon compounds, to their process of preparation and to their use in depositing a self-assembled monolayer of these compounds at the surface of a solid support. The present invention also relates to the solid supports thus modified and to their process of preparation, in addition to their use in the synthesis or immobilization of biomolecules.
An organized self-assembled monolayer (SAM) is defined as an assemblage of molecules in which the molecules are organized, which organization is due to interactions between the chains of the molecules, giving rise to a stable, monomolecular and well-ordered anisotropic film (A. Ulman, Chem. Rev., 1996, 96, 1533–1554).
These self-assembled monolayers, which can be obtained reproducibly (J. B. Brozska et al., Langmuir, 1994, 10, 4367–4373), have the distinguishing feature of forming a dense and homogeneous film which is resistant to chemical treatments (acidic or basic).
The formation of SAM on solid supports, for example using octadecyltrichlorosilane, makes possible the preparation of homogeneous organic surfaces with well defined parameters, both chemically and structurally. These surfaces can act as two-dimensional models for fundamental studies, in particular as regards self-assembling phenomena and the chemistry of interfaces (A. Ulman, ibid).
Various organosilicon compounds have been used as coupling agents for the functionalization of solid supports (L. A. Chrisey et al., Nucleic Acids Research, 1996, 24, 15, 3031–3039, U. Maskos et al., Nucleic Acids Research, 1992, 20, 7, 1679–1684) with the aim of immobilizing oligonucleotides or of synthesizing them in situ. However, the organosilicon coupling agents used in these studies form nonhomogeneous films which have very little resistance to the subsequent chemical treatments for the synthesis or immobilization of oligonucleotides. Furthermore, the formation of the films with these coupling agents is not reproducible.